I'm a financial journalist and author with experience as a lawyer, speaker and entrepreneur. As a senior editor at Forbes, I have covered the broad range of topics that affect boomers as they approach retirement age. That means everything from financial strategies and investment scams to working and living better as we get older. My most recent book is Estate Planning Smarts -- a guide for baby boomers and their parents. If you have story ideas or tips, please e-mail me at: deborah [at] estateplanningsmarts [dot] com. You can also follow me on Twitter

Facing our mortality is one of the hardest things we must do in life—so hard, that I postponed my own estate planning even though I’m a lawyer who does this for a living. My husband and I only signed the necessary documents because it was a requirement for adopting our daughter in 2002. And we did that at the airport on the morning we waited for her to arrive from Korea.

To help implement your wishes, trusts and estate lawyers need to ask very tough questions. Some of them might make you squirm. Thinking about the following issues in advance can help you prepare for a meeting about your estate plan.

1. Who will raise your children if both parents die?

A number of clients have told me that they waited until all of their children were grown to discuss estate planning because they couldn’t figure out whom to name as a guardian. Beastie Boys rapper Adam Yauch and his wife came up with an unusual arrangement (see “Adam Yauch’s Will Reveals His Private Dilemma“). If you fail to name a guardian, then the court will do it for you, based on what it deems to be in the best interest of your child. Unless you have confidence that a judge who never knew you has better judgment than you do about matters involving your children, it is best not to stick your head in the sand for 18 years.

2. What if you all die in a common disaster?

Even if you are certain about where you want your estate to go – commonly to a spouse or partner, followed by descendants – you need to address what I call the “God Forbid Clause.” I instinctively reach for the box of KleenexKleenex as I ask it. For some clients the natural answer is “my parents,” “my siblings” or a particular charity. For others it raises issues that could take years of therapy to sort out. A client may be estranged from his or her family; not have other close friends; or have been too busy to develop a commitment to a charitable cause. For these people, addressing this remote possibility becomes the biggest stumbling block to completing an estate plan.

3. Are there any other descendants you haven’t yet mentioned?

A colleague of mine was approached at her mother’s funeral by a woman who was her spitting image. It turns out this woman was my colleague’s half-sister—her mother’s daughter from a prior marriage that her mother had kept a secret.

So if your lawyer asks more than once if there are any other descendants he or she needs to know about, it isn’t because the lawyer forgot about just asking the same question. Sometimes it isn’t until the third time that I have had clients disclose to me a lot more than they put down on my questionnaire, and the estate plan takes on a whole new dimension.

When a husband and wife consult me jointly, I have from time-to-time received calls days later with a revised answer to my question about other descendants. It is critical that, in lawyer-speak, you disclose all of the potential “objects of your bounty.” If you don’t, they will pop-up–if not at your funeral, at some time in the future–and at a greater emotional and financial cost.

4. Have you told me about all the important relationships in your life?

Charles Kuralt had an intimate companion for 29 years who remained a secret from his wife and children. After he died, they became embroiled in a a six-year, public court battle over land in Montana.

Whether you are married or single, your lawyer may prod and ask if you are in a relationship with someone and if it has a legal status such as civil union, domestic partnership or even a same-sex marriage. There may be legal obligations that come with these relationships that you need to know about.

Your lawyer can’t educate you about the rights and obligations unless they have the full picture. I have asked for copies of divorce decrees only to have a client realize that he or she never actually did get around to finalizing a divorce. Again, unless you are leaving everything to the person you are married to, this is information your attorney needs to know or a long drawn-out lawsuit could erupt after your death, consuming your estate in legal fees. You might think that this is what lawyers hope for, but it truly isn’t. It is a hard way to make a living and an even harder way to watch someone’s legacy destroyed.

5. Do you have genetic material on ice?

When thinking about children and descendants, science is pushing the boundaries of those definitions. Even if the lawyer doesn’t ask, you should disclose “what’s in the freezer.” In other words, do you have genetic material, such as fertilized embryos, eggs, or sperm, preserved for later use? If you do, it is critical to consider whether you want to provide for beneficiaries conceived after your death. And if you do, for how many years do you want to leave the window open for that birth to take place?

There are legal and logistical limits and complications to work out and your wishes might not be possible to carry out. But they should be openly discussed with your estate planner. Litigation involving children conceived after the death of a legal parent and ownership of genetic material are hot areas of litigation that could be avoided if disclosed, discussed and agreed upon ahead of time.

6. Are you transgender?

You may not want to disclose that you are in the midst of gender transition, or that you have been through one already. But there are legal implications that need to be considered if this is the case. Again, even if your lawyer doesn’t ask, this is something that you should bring up. It is critical to ensure that all of your legal documents and the gender identification contained in them reflect how you now present yourself. If there are mismatches, it may be necessary to change your birth certificate (for a summary of name change rules and procedures in the U.S. and Canada, click here), Social Security Registration, driver’s license, passport, security clearances, professional licenses and any other forms of identification you may have. (See “How I Became The Straight Lady For Gay Marriage.”)

7. Have you have ever made large gifts to others?

Often this is a question that we don’t want to think about, especially if we are supporting family members or friends who have fallen on hard times, aren’t able to support themselves, or got into financial trouble. This can be a difficult issue between couples who disagreed about making a gift that the other made.

Your lawyer isn’t asking this question to be nosy. Most gifts in excess of $13,000 per person, per year need to be reported on a federal gift tax return (and maybe even a state gift tax return in Connecticut and Tennessee). The gift might not actually be taxable, but it may still need to be reported. So, your lawyer can help you correctly report past gifts and get you back on track for future ones. We can also advise you on techniques to mitigate reporting and/or tax consequences. It is important to get this information on the table to get the advice you need to defend an audit down the road.

8. Who is going to take care of your pets?

You may not need to set up a full-blown pet trust, but you may need to set aside sufficient funds to be put in trustworthy hands to take care of Fido. If you have racehorses or animals with long life expectancies, you may need more sophisticated planning, including a pet trust. Or, if you don’t have someone you can rely on to take on your pets, especially if you have 17 cats or even two spiders, you will need to find an organization to take care of your companions for the remainder of their natural lives. Your estate planner can help you do this. (See “If You Love Your Dog–Or Cat Or Gerbil–Read This”).

9. When do you want the plug pulled?

Almost certainly your lawyer will ask you to sign a health care directive concerning the withholding of nutrition and hydration. Susan T. Bart of Sidley Austin LLP in Chicago suggests that this is a good time to dig deeper into our souls and think about timing and under what circumstances. We each have a definite idea as to when quality of life has diminished too far. It is helpful to share that information with your healthcare agent who has to be a part of carrying out instructions. If you don’t share that information, people may let loved ones linger on when if they had had more insight they might have ceased aggressive medical intervention sooner. (See “Should I Stay Or Should I Go? What Religion Says About Pulling The Plug.”)

10. What are your passwords, user names and security questions?

Until a few years ago, we didn’t really worry about your digital life. Your e-mail and Facebook accounts will go dormant. But some folks have self-published books that are only accessible on line, journalists and photographers may have their life’s work on a hard drive or saved in cloud storage. Plus there could be bank accounts you only receive e-mail statements for, blogs, Twitter, photo storage, and countless other financially and emotionally valuable assets accessible only by computer.

Your lawyer can help you figure out what needs to be preserved, what can be left to lapse, and who should be able to access these various accounts. There are a number of cloud storage sites, such as Dropbox, where you can store your passwords, and then you only need to give someone the password to access that information. Alternatively, you can leave the password to access your personal information in a safe deposit box or with your lawyer. Dealing with digital property is still in its infancy, and technology is ever changing, so there are no perfect solutions. But you and your estate-planning lawyer can explore the options and pick the one you are most comfortable with for now. (See “Six Ways To Store Securely The Keys To Your Online Financial Life.”)

11. Did you enter into a prenuptial or postnuptial agreement or did you sign a community property agreement?

These documents may be long forgotten and long ignored as irrelevant. But after your death, a disgruntled heir could surface them and derail your best estate planning intentions. Even if you don’t consider them relevant any more, disclose them. If they really aren’t relevant, your estate planning attorney can help you legally terminate them. But to provide that assistance, the lawyer has to know that the documents exist.

12. Have you had any serious or chronic health issues?

You might not think this is relevant to estate planning. No, your attorney isn’t wondering if he or she needs to put off a vacation for your imminent probate. Rather, a lot of sophisticated planning is based on actuarial life expectancies. The reality is that those techniques are only useful if the actuarial tables approximate what we think to be true. If you have particular health concerns or health conditions that could change assumptions of life expectancy, we would plan differently.

Whether or not your lawyer concludes with the catchall question, “Is there anything else I should know?” don’t be afraid to speak up. Chances are you’ve covered a lot of territory. Conversations can be circular, rather than linear. Maybe you started to say something and got distracted. Or perhaps you haven’t gotten to something you expected to cover. That additional little detail might not be relevant. Or it might make all the difference.

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I’ve read such columns for decades (yes, that is well over 19 years) now and normally, the ideas are all the same, stale, and ages old and if you’ve never read such an article, well, then they are useful. Normally not.

However, I am impressed with the thinking of this woman. She offers new ideas and new techniques for a new age.

What about….”have you spoken with your heirs about the terms of your plan?” Too much planning is done in secrecy, unnecessarily. When the heirs have a chance to talk with you about it, many of the later problems, like sibling wars can be avoided. The parents have a chance to explain their thinking, the heirs have a chance to express their feelings and the whole family has a chance for a meaningful dialogue. Dr Mary Gresham www.atlantafinancialpsychology.com

Wendy, this is a great list and would make a great checklist to ask your clients during an initial interview. As an estate planning attorney myself, I ask these questions on a daily basis, but even I found one that I’d never approached with a client before: #6 Are you Transgender? Thanks for sharing your insight.

These questions are definitely necessary when planning for the future. But where can you go to document all this information? Even once all these questions have been legally documented do the appropriate family members and friends know where the paperwork is located? This article presents a good place to start but there are much more in depth issues that have to be addressed. Maria from speedyloansearch.com

I practice here in California, where the issue of Community Property is directly tied to capital gains taxes. I am helping a client administer her husband’s estate. Even though they are worth a combined $10 million, her husband didn’t feel the need to hire an attorney to draft their documents, but used a non-attorney trust mill.

On his death, it was discovered their primary residence was not held in community property at all. During a refinance, it got deeded out to Joint Tenancy, and never put back into his Trust.

This proved to be a costly mistake, as he lost out on the full stepped-up basis available to assets held as community property. The wife now wants to sell their residence, but is facing a six-figure tax bill for capital gains.

As the Estate and Gift Taxes fade from discussion due to the $10.24 million credit per couple, the Capital Gains Tax become even more important. In California, Capital Gains are taxed like Ordinary Income, meaning long-term gain can still be subject to nearly 30% tax.

As an estate planning attorney for over two decades, I want to thank you for posting informative and thoughtful columns that help educate the public.

Most estate planning remains stubbornly traditional and old-fashioned and does not take into consideration 21st Century issues, culture and values. It’s high time for the entire estate planning community to address the impact divorce, blended families, remarriage, increased longevity, alternative lifestyles, affluenza, personal debt, bankruptcy, lawsuits, and incapacity, among others, has on individuals and families.

I appreciate Ms. Goffe’s column and her approach with her clients. I would add one critical squirmy question, however, and that’s who should take care of the children if both parents become incapacitated – but don’t die.

As this is the statistically more probable situation than having both parents die, we designed an efficient, practical and compassionate solution. We recommend that parents appoint a panel of loved ones (a “Guardianship Panel”) who will name Disability (temporary) Guardians for their minor children if the parents become incapacitated, and Permanent Guardians if the parents are deceased. The Panel is flexible, modern and solves the age-old parents’ dilemma of deciding in the present who would be the right guardian in the future. While permanent guardianship is dealt with in the parent’s will, parents can include Disability Guardianship provisions in a living trust or a durable power of attorney, which are effective during lifetime. We put the same provisions in both documents and have parents include a separate Letter of Instruction with timely, updated and detailed information for the panel members and appointed guardians to consider. The peace of mind this arrangement provides parents is priceless.

I’d like to add to number 1, make sure in the cold light of day the guardians you’ve nominated in your will mean it. Truly mean it. These is not a twice-yearly-greeting-card-with-cash godparent notional agreement. It’s the real deal and sometimes that number gets called. In the very least, interview them like you would a nanny. These are the people who will take care of your child. Make sure they’re on board. For real.

When my mother died twelve years after my father, everything was perfectly arranged. The trust fund was in place, the will and codicils were all in order, there were no creditors. But the two couples, decent family friends, both ‘declined to serve’ as my guardian. My grandmother was in ill mental health due to the death of her only child and in the judges chambers, my 14 year-old self became the legal ward of my equally shell-shocked 18 year-old sister.

You can make all the financial arrangements you want. You can feel secure in your watertight planning, but if a child doesn’t have someone committed to minding the store and no one steps in, bad things can happen. And that financial security will just make them more of a target. I’m now 33 and still struggle daily with profound arrested development from my adult-free latter childhood.